Getting co(m)fortable with anal!

Hello all, I'm a senior in college who despite considering myself to be hetero, I love the feeling of anal play. I know this isn't anything new or even that unique, lots of guys do this and it's perfectly normal. So I'm not writing this because I'm unique, I'm writing it in the hopes that someone else out there that was unconfident like me, gets the courage and reassurance ti try it out!

I had tried anal play off and on several times starting in middle school. It had started with fingers and butt sharpies (stick to fingers or real sex toys, don't risk a trip to the er). I would try it and slightly enjoy it, but then I would supress it out of embarassment, and not try again for months. Finally at some point I gathered the courage to get my first sex toy. I got it at Spencers gifts, a simple vibrator, because they apparently weren't too tight on there carding policy. The buzzing feeling made me once and for all reconcile that I liked the feeling, but the social stigma was still there, so I got rid of it. After that I'd had conversations with two of my closest friends, females, about the topic. They were supportive and one of them actually gifted me a vibrator to try again after I had gotten rid of my first one out of embarassment. This was when I started becoming comfortable with it.

The day he owned me [M/F]

I've never been in any type of Dominant/Submissive relationship. That is, until I met him. I've never had someone assert themselves over me quite the way he has and to be honest, I wasn't sold on the idea at first but I tried and I'm glad I did. The day he owned me started out like any other. Texts were exchanged, quite a bit of eye fucking, stealing little touches here and there, the usual in our gloriously uncomplicated friendship. We made plans for him to stop by and I had a little surprise up my sleeve. As a tease I dressed up in my black lace up corset, black lace garter belt, thigh high stockings and my stilettos. I'm 5'9" and curvy where it counts with DD tits (all real). When I opened the door I could tell by the look on his face all bets were off. He stepped in, locked the door then turned around to face me. He said "What's this?" Waving his hand up and down my body. To which I replied, "I thought I'd tease you." "You thought you'd tease me, what?" "I thought I'd tease you, Sir." He took a few steps towards me and placed his fingers on my stomach pushing me backwards towards the wall. The entire time he was looking me up and down with the hottest fucking look on his face I'd ever seen. When he got me to the wall he took his hand off me and commanded me to turn around, face the wall and put my hands on it. He stepped up close enough that I could feel his body heat but the only part of him touching me was his breath on my neck. He then gently pushed my feet apart with his until he got my legs spread to his satisfaction. I felt a shock of electricity that went straight to my pussy when he put his fingertips on the outside of my knee and slowly slid them all the way up and to the inside of my thigh. He stopped at the top of my thigh highs and slipped a finger under the lace, popping it as he withdrew. He wrapped his other hand around my throat and tilted my head back towards his and growled his approval at my appearance into my ear. He released my neck and said, "Put your forehead on the wall and do not move until I give you permission." His hands where on my back moving down the corset and stopped at my garter. He pushed his thumbs through the garter tearing it. He threw it on the ground and mumbled under his breath, "it was just in the way." His hands were on me again exploring every inch of my ass. He grabbed my hips and pulled them towards him, putting my naked ass and waxed pussy on full display for him. His fingers found my warm, wet slit and he began to tease my clit mercilessly but never dipped his fingers in. I could tell he was fighting to keep his self control because the more he started to lose it, the harder he dug his fingers into my hip he was holding. I was desperate for release and started trying to press my pussy harder onto his hand, but he wasn't going to let me have it. He leaned in close to my ear and said, "You sound sexy as fuck when you moan for me. Do you want me to own your ass?", as he ran his pussy soaked finger up to my ass and forced one in. He grabbed me around my shoulder with his free hand and pulled my upper body to his as he was fingering my ass. I was so fucking hot I wanted more and started grinding down on his finger. That unraveled what little self control he had left and with a sudden jolt he slammed me back against the wall, pulled his finger out of my ass, slapped my ass cheek and told me to put my hands back on the wall and not move them. As I complied with his commands I could hear him make quick work of undressing. He needed to own my ass almost as much as I needed him to at that point. I felt his hard cock slide slowly between my wet pussy lips to my clit where he teased it for a minute before he slid his cock into my hot, wet hole. When he was in, he stood still and as my pussy was trying to acclimate to his size. "You feel fucking amazing." With his admission I squeezed down on his cock and he immediately grabbed my hair at the nape of my neck, yanked back and said "No." With that he pulled out of my pussy and positioned himself at my ass. He teased me with his tip dripping with pre cum to get me to open up for him. Inch by agonizing inch he started to enter my ass. I couldn't stand it any longer so I used the leverage from the wall and push my ass down on his cock. All the way down. I did it so fast he didn't register what was going on for several seconds. It was painfully sweet as I started to move. I was undoing him one rotation of my hips at a time and he loved it. But I was disobedient and he let me know. He grabbed my neck, pulled my head back to his and said, "You think you can do what you want? You will not breathe until I allow it and you will not stop moving on my cock." He made good on his threat, squeezing my throat until I could no longer breathe and he started to move with me. I was able to let a moan escape despite my lack of oxygen which sent him over the edge he was desperately trying to hold onto. Slamming into my ass as hard as he could, he released my throat , gripped my hip with one hand and pushed me back onto the wall with his other. With every stroke, I was screaming his name begging him for more. He needed release as much as I did, but my punishment wasn't over yet. He reached around between strokes and slapped my clit….hard…it sent me into the most painful and mind blowing orgasim of my life. My pussy was clinching so hard he could feel it which made him explode in my ass. He rested his head on my shoulder and put his hands over mine on the wall and whispered "fuck" several times before he pulled out of me……he owned me.

[Getting off at work/in public UPDATE] Giving a blow job in the cigar bar parking lot. (m/f)

First story here: https://www.reddit.com/r/gonewildstories/comments/3sp9fd/getting_off_at_workin_public_for_the_first_time/

(Some sexy stuff in the lead up, but jump to the mark below for the payoff)


Dan had made it clear he was too nervous to make the first move. I took the initiative and he came over last Saturday for "debating over a bottle of wine." (What can I say, we're both turned on by intelligence and our most sexually charged moments have been when disagreeing with each other on an intellectual topic.)

When he came over on Saturday night he looked a little pale and ran to the bathroom twice in the first twenty minutes or so. I was sitting on the couch thinking, Great. If he's sick there's no way anything is going to happen tonight. (He would tell me later he had lied and was not sick at all, just nervous as fuck, haha.)

Despite thinking he wasn't feeling great, I made the move from my couch to his, snuggling in close. Half an hour later of being as forward as possible, he suddenly grabbed my face and kissed me without any warning. Mercifully my roommate was out for the night and we quickly went to my room.

[M]y [F]riend’s Girlfriend

Back in my university days I had a friend who had a girlfriend who was the worst thing ever. She would nag at him while we were hanging out. She was this small town girl who if I ever cursed she would make a face and tell me not to do that. I mean every single time. She would purposely complain about whatever when I was around. It drove me nuts.

She was attractive. She was a good height, fair skinned, with small sized breasts and a nice ass. She wasn’t drop dead gorgeous or anything but if she wasn’t so annoying I would be attracted to her.

She dated my friend for what seemed like 3 years throughout college. They would be on and off again. Get into some fight he would ask me for my opinion. I would give it to him. Whenever they were fighting I would be completely honest with him and tell him that she was the most annoying girl I knew. But he would always end up getting back together with her.

Best 24+ hours of my life – losing virginity [M/F]

So I didn't think I'd be writing anything like this for a while. I've always been quite shy, don't drink or go out much, and up until just over a week ago I was a 27 year old kissless virgin. But somehow, with very little effort on my part that has now finally changed. Mostly writing this so I can try and remember it all. Changed the names – It might be a little long, but hopefully it'll show other quiet guys it can happen.

I was travelling on a group tour in S.E. Asia with about 15 other people. We'd been travelling together for about 4 weeks, but as I'm a quiet guy I didn't really speak to her much (I'll call her Kate). She didn't really catch my eye properly at first, but the longer we travelled together, the more I liked her. She was 26, fairly attractive (nice curves), pretty outgoing, very funny and one of the more fun people to be around.

Skinny dipping with a friend[M] leads to me[F] losing my virginity

I'm a bit of a rambler, and a long time lurker… I never thought of posting on reddit until I came across this sub! Being a frequent visitor, I finally mustered up the courage to refine and recount my own tale. So I'm going to tell a long stoy of me losing my virginity a few months back, with a lot of juicy detail! Hope you enjoy ;)

If you want to get to the hot and heavy bits, scroll down until you see


I'm a small 19 year old girl, asian background, 5"2', with a small waist, a round ass made from squatting and a perky pair of full B cup boobs. I grew up in a church community and in an all-girls school, and so had very little interaction with guys that I consider romantic or sexual. But I've been sexually curious and explored many channels of relief for a while now, which I kept a secret from everyone but my best friend.

Mother’s Little Helper: Chapter 1 [M/F] [drugs] [prost] [reluc]

Mother's Little Helper
Fiction by Evil Little Sister

Part One – Chapter 1

Up at five thirty, in and out of the bathroom, downstairs to start breakfast. Jack's up by six and I can hear him shuffling around upstairs. I have to get back up there, rousing Amy first, my daughter, frowning at me, disliking me because I'm her mom and she's fifteen and hates me. Into Jack Junior's room, JJ, who's all of nine and smiling first thing, blinking as I hurry him out of bed. Into the nursery, getting Jilly up, she's going to need the potty right away. She's three and my little angel and she just needs some hand holding going down the stairs.

Jack's got the wrong tie and I give it a tug and shake my head as we pass. He's running late, as always, and so am I. So are the kids. I'm yelling, begging, threatening, getting everyone dressed and into the kitchen. Amy doesn't want to eat. She's getting fat. The boys won't like her if she has a little toast. JJ wants the chocolate cereal, not the one with the Tiger on it. Jilly is making a snowman out of her instant oatmeal.

An old story – closest thing I’ve ever had to a threesome. [mf]

This is a story from the year after I left university. It’s the closest thing I’ve ever had to a threesome.

I’d been invited to a house party in a big shared house in Putney, where lots of my friends lived. I was single at the time but there was a guy at the party I’d slept with a couple of times, in a friends-with-benefits kind of way. Let’s call him Paul (for the sake of argument).

Paul and I hadn’t had sex for a few weeks and I wasn’t sure it would happen again – though I was hoping it might. The party went on with lots of laughing and dancing and we chatted a bit, always with others nearby so there were no clues whether he had sex on his mind or not.

I’d been half hoping we might end up going home together, to my place or to his, but it got late and it was clear that lots of us were going to end up staying over, as we often did after parties in those almost-student days.

The virgin slut (Dept store fantasy Pt. 3) [M/f] [virgin] [slight-Fsub]

After learning the girl who I had an amazing sexual encounter with was my bosses daughter, I had no idea what to do. My options were to either tell her…which wasn’t going to happen, cease all contact with her…also not an option, or just not tell her and pretend nothing had changed. Obviously, I opted for the last one. After my little meeting with him, I had a pretty hot conversation with her after the picture, and ended up jerking off in the bathroom at work just to be able to finish my day. The topic of meeting up kind of disappeared that day, and hadn’t come back up since. At first I was relieved, since I was unsure what to do with this whole insane situation, but after just a couple days, and after I made my decision, it was all I could think about all over again. So when my boss came to me that Friday to let me know he was going to be gone for the entire weekend and a few days the following week, and wanted to dump a bunch of extra work on me, I didn’t even mind! It just put ideas in my head…

I liked his smile, [M/F] [office] [public] [consensual rape]

I liked his smile. That is how it all started. He looked like the real deal, tall, kind eyes, safe. He was kind too, he had this voice that said everything was going to be ok. We were all new and of all the teachers in our training groups I liked him. So we took our places at the cubicles and turned on our computers, I kept an eye on him because I wanted to be in his group. As it turns out I had nothing to worry about, he was in charge and that was that. You know how when you start liking someone and start sitting straight so you dont look like a slob? Well….. That. Yes, I had it bad. I couldn't even hear what he was saying, ny heart was beating loudly and ny insides felt coiled around ….aroooouuund… idk, thought processes .exe